CN105237595A - N2-glycosyl-substituted 1,2,3-triazole compound and synthesis method and application thereof - Google Patents
N2-glycosyl-substituted 1,2,3-triazole compound and synthesis method and application thereof Download PDFInfo
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Abstract
The invention relates to an N2-glycosyl-substituted 1,2,3-triazole compound and a synthesis method and application thereof. The general structural formula of the N2-glycosyl-substituted 1,2,3-triazole compound is shown in the specification, wherein R1 indicates H atoms or halogen atoms or alkyl groups of 1-6 carbon atoms or alkoxy groups of 3-10 carbon atoms or aryl groups or heterocyclic groups or benzoyl groups or formyloxy groups or cyano groups, and R indicates hydrogen or alkyl groups or halogen atoms or nitro groups or alkoxy groups or cyano groups and is located at ortho-position, meta-position and para-position single substitution or polysubstitution of aromatic rings. The N2-glycosyl-substituted 1,2,3-triazole compound and the synthesis method and application thereof have the advantages that synthesis conditions are easy to control, the yield is high, and the cost is low; application of triazole derivatives in the fields of pesticide, medicine, food and the like is further promoted; a new way is provided for research and development of high-value utilization and modification of triazole; the compound has high inhibiting ability for alpha-glucosidase and can be further developed into medicine used for treating or assisting in treating diabetes mellitus type 2.
Description
Technical field
The present invention relates to 1,2,3-triazoles compound and synthetic method and application that N2-glycosyl replaces.
Background technology
1, 2, 3-triazole is as the important heterogeneous ring compound of a class, because of the physico-chemical property that it is special, as 1, 2, 3-triazole ring is the isostere of amido linkage, metabolic is explained, redox and have good stability under acid or alkali environment, and can hydrogen bond action etc. be participated in, these character make triazole ring be conducive to combining with biomolecular targets, put forward high molecular solvability simultaneously, thus in agricultural, medicine, life science, materials chemistry, the fields such as Synthetic Organic Chemistry are all widely used, have now found that some 1, 2, 3-triazole compounds has biological activity in medical, a large amount of 1, 2, 3-triazole compounds is found to have potential antibacterial, analgesia, anti-inflammatory, toponarcosis, spasmolytic, antitumor, anti-malarial, antiviral and anticancer work.
Therefore, 1,2,3-triazoles ring has very large pharmaceutical potential as the bioactive Medicinal molecular fragment of structure, and Design and synthesis novel 1,2,3-triazoles compound is pharmaceutical chemical study hotspot.
Sugar is indispensable energy derive in life entity, and its katabolic product can be the materials such as the interior synthesis of human body some amino acid, fat, protein and cholesterol and supplies raw materials.Simultaneously due to constructional feature and the good biocompatibility of saccharide compound, be now widely used in pharmaceutical chemical research.
Because saccharide compound is mostly polyol, better water-soluble, if combined by good to itself and biological activity heterogeneous ring compound, the water-soluble of heterogeneous ring compound can be improved so that better absorb by human body, play maximum drug effect.Secondly, because saccharide compound has special physiological function, usually can be used as the target spot of medicine, if combined with saccharide compound by the heterogeneous ring compound with good biological activity, the targeting of heterogeneous ring compound thing to certain virus can be strengthened.Again, the heterogeneous ring compound containing glycosyl may be inhibited to the enzyme producing some disease.Therefore, how to connect carbohydrate and heterogeneous ring compound to generate novel cpd, in medical, there is important researching value.
In a kind of body of diabetic history Regular Insulin relatively or definitely not enough or target cell insulin sensitivity is reduced, or a kind of chronic disease of carbohydrate, fat and protein metabolism disorder that Regular Insulin itself exists structural defect and causes.Its principal feature is hyperglycemia, glycosuria.Clinical signs is many drinks, many foods, diuresis and lose weight (i.e. " three-many-one-little "), some tissues or organ generation morphological structure can be made to change and dysfunction, concurrent ketoacidosis, extremity gangrene, polyneuritis, blind and renal failure etc., this sick sickness rate increases day by day, the common disease that become international, frequently-occurring disease.
Current 1,2,3-triazoles glycoconjugate has reported to have biological activity, but present reported 1,2,3-triazole glycoconjugate is 1,2 of N1 or N3 replacement, 3-triazole compounds, it synthesizes [3+2] cycloaddition click-reaction based on Terminal Acetylenes and organic azide, does not have N2-glycosyl to roll into a ball replace 1,2,3-triazole compounds, its research is a blank.
Summary of the invention
Main purpose of the present invention is be the N2-glycosyl replacement that proposition one class is novel 1,2,3-triazole compounds, and the synthetic method of this compounds is provided simultaneously, it is perfect glycosylated 1, the research of 2,3-triazole compounds, all significant in methodology of organic synthesis and pharmaceutical chemistry.This compounds has stronger rejection ability to alpha-glucosidase, can be developed as further and be used for the treatment of and the medicine of assisting therapy diabetes B.
It is as follows that the present invention solves the problems of the technologies described above adopted technical scheme: the 1,2,3-triazoles compound that N2-glycosyl replaces, and its general structure is as follows:
Wherein: R
1for the alkoxyl group of the alkyl of H atom, halogen atom, 1 ~ 6 carbon atom, 3 ~ 10 carbon atoms, aryl, heterocyclic radical, benzoyl, formyloxy or cyano group; R is hydrogen, alkyl, halogen atom, nitro, alkoxyl group or cyano group, and be positioned at aromatic ring neighbour, contraposition monosubstituted or polysubstituted.
The 1,2,3-triazoles compound that N2-glycosyl replaces, its general structure is as follows:
Wherein: R
1for the alkoxyl group of the alkyl of H atom, halogen atom, 1 ~ 6 carbon atom, 3 ~ 10 carbon atoms, aryl, heterocyclic radical, benzoyl, formyloxy or cyano group; R is hydrogen, alkyl, halogen atom, nitro, alkoxyl group or cyano group, and be positioned at aromatic ring neighbour, contraposition monosubstituted or polysubstituted.
By such scheme, described aryl is phenyl or by F, Cl, Br, I, CN, NO
2substituted-phenyl.
By such scheme, described heterocyclic radical is pyridine, pyrimidine, quinoline or isoquinoline 99.9.
By such scheme, the 1,2,3-triazoles compound that described N2-glycosyl replaces is raceme, R type isomer or S type isomer.
The preparation method of the 1,2,3-triazoles compounds that described N2-glycosyl replaces, includes following steps:
By 1,2,3-triazoles compounds and 1-methyl-2; 3-O-isopropylidene-5-O-p-toluenesulfonyl-D-RIBOSE joins in round-bottomed flask, adds a small amount of alkali, adds solvent; under 70 DEG C ~ 100 DEG C conditions, react 6h, after reaction terminates, stop heating; be extracted with ethyl acetate, extract organic phase, again use saturated common salt water washing organic layer; then use anhydrous sodium sulfate drying organic layer, filter, concentrating under reduced pressure obtains 1 of the replacement of N2-glycosyl; 2,3-triazole class compounds.
1 of described N2-glycosyl replacement, 2, the preparation method of 3-triazole class compounds, include following steps: by 1, 2, 3-triazole class compounds and 1-methyl-2, 3-O-isopropylidene-5-O-p-toluenesulfonyl-D-RIBOSE joins in round-bottomed flask, add a small amount of alkali, add solvent, 6h is reacted under 70 DEG C ~ 100 DEG C conditions, after reaction terminates, stop heating, be extracted with ethyl acetate, extract organic phase, again use saturated common salt water washing organic layer, then anhydrous sodium sulfate drying organic layer is used, filter, concentrating under reduced pressure obtains 1 of the replacement of N2-glycosyl, 2, 3-triazole class compounds, join in rare aqueous acid, react two days under 70 DEG C ~ 100 DEG C conditions, after reaction terminates, stop heating, be extracted with ethyl acetate, extract organic phase, again use saturated common salt water washing organic layer, then anhydrous sodium sulfate drying organic layer is used, filter, concentrating under reduced pressure obtains 1 of the replacement of N2-glycosyl, 2, the hydrolysate of 3-triazole class compounds.
By such scheme, described solvent is DMF, DMSO or acetonitrile.
By such scheme, described alkali is salt of wormwood or sodium carbonate.
By such scheme, described diluted acid is sulfuric acid.
Active testing; All compounds all carry out alpha-glycosidase active testing, and testing method is:
Use all general formula compound I and general formula compound II to be substrate, carry out in phosphoric acid buffer (pH6.8).Add enzyme when 0-5 DEG C, start reaction afterwards.Sodium carbonate termination reaction is added after 37 DEG C of reaction 15min.The ultraviolet absorption value of solution is read at 490nm place, and computerized compound inhibiting rate.
The advantage that the present invention has:
1) the present invention obtains the glycosylated 1,2,3-triazoles derivative of novel N2 by effective synthesizing mean, and synthesis condition easily controls, and productive rate is high, and cost is lower;
2) after the present invention introduces glycosyl, improve the water-soluble of triazole compounds, triazole derivative can be improved further at agricultural chemicals, medicine, the use in the fields such as food;
3) the present invention connects with in triazole by stable C-N top-notch player's glycosyl, fill up N glycosylation and replace 1,2, some of 3-triazole compounds are blank, for based on 1, the pharmaceutical chemistry research of 2,3-triazole heterocycle compound provides theoretical and actual guidance, and the research and development of modifying for triazole higher value application open a Tiao Xin road.
4) the present invention is based on the synthetic route that active superposition theorem obtains, structural modification is carried out to D-ribose that is nontoxic, natural reproducible, by structures to form, the triazole group of high bacteriostatic activity is introduced in D-ribose molecule, obtain there is amphipathic one containing 1, the glycosyl derivatives of 2,3-triazole.
5) this compounds has stronger rejection ability to alpha-glucosidase, can be developed as further and be used for the treatment of and the medicine of assisting therapy diabetes B.
Embodiment
Below in conjunction with embodiment, the present invention will be further described, but can not as limitation of the invention.
The synthesis of 1-methyl-2,3-O-isopropylidene-5-O-p-toluenesulfonyl-D-RIBOSE
Get D-ribose to be suspended in the mixed solution of anhydrous propanone and anhydrous methanol, add anhydrous magnesium sulfate and tosic acid in 40 ~ 45 DEG C of stirring reaction 4h; Filter, extraction into ethyl acetate, obtains light yellow liquid; In this yellow liquid, add triethylamine, drip the anhydrous methylene chloride solution containing Tosyl chloride, drip and finish at 0 DEG C, 0 ~ 5 DEG C is stirred 5h, adds water and stirs 30min, extraction, concentrating under reduced pressure, and enriched material dehydrated alcohol recrystallization, obtains white solid;
Reaction equation is as follows:
The synthesis of 1,2,3-triazoles
Be dissolved in by sodiumazide in DMSO, heated and stirred, be dissolved in DMSO by phenyl nitro olefin(e) compound, be slowly added dropwise in sodium azide solution with constant pressure funnel, control rate of addition, temperature of reaction is 80 DEG C.After dropwising, stop heating, be extracted with ethyl acetate, extract organic phase, again use saturated common salt water washing organic layer, then use anhydrous sodium sulfate drying organic layer, filter, concentrating under reduced pressure obtains brown solid.Be obtained by reacting the triazole 5 having replacement more further.
Reaction equation is as follows:
The synthesis of 1,2,3-triazoles glycoconjugate
By 1,2,3-triazoles compounds and 1-methyl-2; 3-O-isopropylidene-5-O-p-toluenesulfonyl-D-RIBOSE joins in round-bottomed flask, adds a small amount of alkali, adds DMF and make solvent; react under the condition of 70 DEG C ~ 100 DEG C, reaction 6h, after reaction terminates; stop heating, be extracted with ethyl acetate, extract organic phase; again use saturated common salt water washing organic layer; then use anhydrous sodium sulfate drying organic layer, filter, concentrating under reduced pressure obtains general formula compound I.
Reaction equation is as follows:
General formula compound I is joined in rare aqueous acid, react two days under 70 DEG C ~ 100 DEG C conditions.After reaction terminates, stop heating, be extracted with ethyl acetate, extract organic phase, again use saturated common salt water washing organic layer, then use anhydrous sodium sulfate drying organic layer, filter, concentrating under reduced pressure obtains general formula compound II.
Reaction equation is as follows:
Embodiment 1
Step 1: compound a
1synthesis,
Take sodiumazide (8.7g, 0.13mol) be dissolved in 35mLDMSO, heated and stirred, by phenyl nitro olefin(e) compound (16.63g, 0.11mol) be dissolved in 30mLDMSO, slowly be added dropwise in sodium azide solution with constant pressure funnel, controlling rate of addition is drip one in 3 seconds, and temperature of reaction is 80 DEG C.After dropwising, stop heating and continue to stir, being cooled to room temperature; In mixed solution, add ammonium chloride solution, be extracted with ethyl acetate, extract organic phase, again use saturated common salt water washing organic layer, then use anhydrous sodium sulfate drying organic layer, filter, concentrating under reduced pressure obtains brown solid.Finally wash products obtained therefrom with methylene dichloride with a small amount of principle repeatedly, obtain white solid and be about 14.51g, yield is 91%.
Step 2; Compound b
1synthesis
Get 5gD-ribose (30mmol) to be suspended in the mixed solution of 30mL anhydrous propanone and 10mL anhydrous methanol, add 4g (30mmol) anhydrous magnesium sulfate and 0.3g (2mmol) tosic acid in 40 ~ 45 DEG C of stirring reaction 4h.Filter, extraction into ethyl acetate, obtains light yellow liquid.4.6mL (33.1mmol) triethylamine is added in this yellow liquid, the anhydrous methylene chloride solution that 30mL contains 5.8g (33.1mmol) Tosyl chloride is dripped at 0 DEG C, drip and finish, 0 ~ 5 DEG C is stirred 5h, the 5mL that adds water stirs 30min, extraction, concentrating under reduced pressure, enriched material dehydrated alcohol recrystallization, obtains white solid (8.63g yield 72.4%).
Step 3; Compound c
1synthesis
Get 124 Triazole (compound a
1) 300mg, 1-methyl-2,3-O-isopropylidene-5-O-p-toluenesulfonyl-D-RIBOSE (compound b1) 878mg, salt of wormwood 600mg.Be added to 100mL round-bottomed bottle, add DMF30mL, be heated to 80, DEG C reaction 6h.Be extracted with ethyl acetate, extract organic phase, again use saturated common salt water washing organic layer, then use anhydrous sodium sulfate drying organic layer, filter, concentrating under reduced pressure obtains faint yellow solid.Ethyl acetate/petroleum ether (1:10) column chromatography obtains white solid, i.e. compound c
1.
1HNMR(600MHz,CDCl
3)δ7.87(s,1H),7.78(d,J＝7.2Hz,2H),7.42(d,J＝7.8Hz,2H),7.35(t,J＝7.2Hz,1H),5.03(s,1H),4.86(d,J＝6.0Hz,1H),4.78(t,J＝7.2Hz,1H),4.71(d,J＝6.0Hz,1H),4.64–4.56(m,2H),3.41(s,3H),1.47(s,3H),1.31(s,3H).
Embodiment 2 ~ 5
The step 1 of the reactions steps reference example 1 of embodiment 2 ~ 5, step 2 and step 3, participate in compound of reaction and be listed as follows:
c
2：
1HNMR(600MHz,CDCl
3)δ7.76–7.62(m,2H),7.57–7.51(m,1H),7.41(t,J＝7.8Hz,1H),7.32(dd,J＝14.4,7.3Hz,1H),5.01(s,1H),4.85(dd,J＝11.4,5.9Hz,1H),4.78–4.73(m,1H),4.69(dd,J＝6.0,2.0Hz,1H),4.54–4.47(m,2H),3.38(d,J＝3.6Hz,3H),2.45(d,J＝16.2Hz,3H),1.44(d,J＝11.4Hz,3H),1.29(s,3H).
c
3：
1HNMR(400MHz,CDCl
3)δ7.68(d,J＝7.8Hz,1H),7.37(t,J＝4.2Hz,2H),7.27(s,1H),5.03(s,1H),4.90(d,J＝6.0Hz,1H),4.76(d,J＝7.2Hz,1H),4.70(d,J＝6.0Hz,1H),4.55(dd,J＝7.2,3.0Hz,2H),3.39(s,3H),2.27(s,3H),1.48(s,3H),1.31(s,3H).
c
4：
1HNMR(600MHz,CDCl
3)δ8.15(s,1H),7.83(d,J＝8.4Hz,1H),7.48(s,1H),7.30(d,J＝8.4Hz,1H),5.03(s,1H),4.87(d,J＝6.0Hz,1H),4.79(t,J＝7.2Hz,1H),4.71(d,J＝6.0Hz,1H),4.62(dd,J＝12.0,7.5Hz,2H),3.41(s,3H),1.47(s,3H),1.31(s,3H).
c
5：
1HNMR(600MHz,CDCl
3)δ7.55(dd,J＝7.2,2.3Hz,4H),7.35(dd,J＝5.4,1.7Hz,6H),5.04(s,1H),4.93(d,J＝6.0Hz,1H),4.84(t,J＝7.2Hz,1H),4.73(d,J＝6.0Hz,1H),4.65–4.59(m,2H),3.42(s,3H),1.47(s,3H),1.31(s,3H).
Embodiment 6
The step 1 of embodiment 6, step 2 and step 3 reference example 1.
Step 4:
By white solid c
6add in dilution heat of sulfuric acid, 80 DEG C of stirrings, react 2 days, TLC monitors reaction, after question response terminates, stops heating, cool to room temperature, be extracted with ethyl acetate, extract organic phase, again use saturated common salt water washing organic layer, then anhydrous sodium sulfate drying organic layer is used, filter, concentrating under reduced pressure obtains faint yellow solid, and ethyl acetate/petroleum ether (1:1) column chromatography obtains white solid.This white solid is compound d
6.
1HNMR(600MHz,DMSO)δ8.14(s,1H),7.76(d,J＝8.4Hz,2H),7.01(d,J＝8.4Hz,2H),5.06(s,1H),4.94(d,J＝6.0Hz,1H),4.62(dd,J＝13.8,3.2Hz,1H),4.47(dd,J＝13.8,8.7Hz,1H),4.22(d,J＝6.0Hz,1H),4.08–4.00(m,1H),3.41(d,J＝10.2Hz,4H).
Embodiment 7
The step 1 of embodiment 7, step 2, step 3 reference example 1, step 4 reference example 6 of embodiment 7.
1HNMR(600MHz,CDCl
3)δ7.99(dd,J＝17.4,7.5Hz,2H),7.77–7.68(m,2H),7.56(dd,J＝15.6,8.2Hz,1H),7.47–7.40(m,2H),7.40–7.31(m,3H),5.30(d,J＝46.8Hz,1H),4.79–4.71(m,1H),4.67(qd,J＝14.4,5.7Hz,2H),4.52(d,J＝5.4Hz,1H),4.12(s,1H),4.00(d,J＝14.4Hz,1H).
Embodiment 8
Active testing:
Sucrose is decomposed into glucose under the effect of alpha-glucosidase, by the growing amount of glucose in determination of glucose oxidase reaction system, calculates trial-product to the restraining effect of alpha-glucosidase.Get need testing solution, be diluted to series concentration.During test, getting respectively is the sample solution 10 μ L of class concentration, add 0.5 μ/mL alpha-glucosaccharase enzyme solution 10 μ L, add 25mmol/L sucrose 10 μ L again, react 15 minutes at 37 DEG C, this reacts on 96 well culture plates and completes, and adopts glucose oxidase method, under 490nm condition, absorbance (A) is measured, using the growing amount of glucose as index calculate inhibiting rate by microplate reader; Choose acarbose as positive control, set blank simultaneously, negative control and sample controls, be calculated as follows:
Inhibition of enzyme activity rate %=[A
negative-(A
sample-A
sample controls)]/(A
negative-A
blank) × 100%
Part of compounds alpha-glycosidase inhibiting rate is as following table:
Claims (11)
- The 1,2,3-triazoles compound that 1.N2-glycosyl replaces, its general structure is as follows:Wherein: R 1for the alkoxyl group of the alkyl of H atom, halogen atom, 1 ~ 6 carbon atom, 3 ~ 10 carbon atoms, aryl, heterocyclic radical, benzoyl, formyloxy or cyano group; R is hydrogen, alkyl, halogen atom, nitro, alkoxyl group or cyano group, and be positioned at aromatic ring neighbour, contraposition monosubstituted or polysubstituted.
- The 1,2,3-triazoles compound that 2.N2-glycosyl replaces, its general structure is as follows:Wherein: R 1for the alkoxyl group of the alkyl of H atom, halogen atom, 1 ~ 6 carbon atom, 3 ~ 10 carbon atoms, aryl, heterocyclic radical, benzoyl, formyloxy or cyano group; R is hydrogen, alkyl, halogen atom, nitro, alkoxyl group or cyano group, and be positioned at aromatic ring neighbour, contraposition monosubstituted or polysubstituted.
- 3. the 1,2,3-triazoles compound that replaces of N2-glycosyl according to claim 1 and 2, is characterized in that described aryl is phenyl or by F, Cl, Br, I, CN, NO 2substituted-phenyl.
- 4. the 1,2,3-triazoles compound of N2-glycosyl replacement according to claim 1 and 2, is characterized in that described heterocyclic radical is pyridine, pyrimidine, quinoline or isoquinoline 99.9.
- 5. the 1,2,3-triazoles compound of N2-glycosyl replacement according to claim 1 and 2, is characterized in that the 1,2,3-triazoles compound that described N2-glycosyl replaces is raceme, R type isomer or S type isomer.
- 6. the preparation method of the 1,2,3-triazoles compounds of N2-glycosyl replacement according to claim 1, includes following steps:By 1,2,3-triazoles compounds and 1-methyl-2; 3-O-isopropylidene-5-O-p-toluenesulfonyl-D-RIBOSE joins in round-bottomed flask, adds a small amount of alkali, adds solvent; under 70 DEG C ~ 100 DEG C conditions, react 6h, after reaction terminates, stop heating; be extracted with ethyl acetate, extract organic phase, again use saturated common salt water washing organic layer; then use anhydrous sodium sulfate drying organic layer, filter, concentrating under reduced pressure obtains 1 of the replacement of N2-glycosyl; 2,3-triazole class compounds.
- 7. N2-glycosyl according to claim 2 replace 1, 2, the preparation method of 3-triazole class compounds, include following steps: by 1, 2, 3-triazole class compounds and 1-methyl-2, 3-O-isopropylidene-5-O-p-toluenesulfonyl-D-RIBOSE joins in round-bottomed flask, add a small amount of alkali, add solvent, 6h is reacted under 70 DEG C ~ 100 DEG C conditions, after reaction terminates, stop heating, be extracted with ethyl acetate, extract organic phase, again use saturated common salt water washing organic layer, then anhydrous sodium sulfate drying organic layer is used, filter, concentrating under reduced pressure obtains 1 of the replacement of N2-glycosyl, 2, 3-triazole class compounds, join in rare aqueous acid, react two days under 70 DEG C ~ 100 DEG C conditions, after reaction terminates, stop heating, be extracted with ethyl acetate, extract organic phase, again use saturated common salt water washing organic layer, then anhydrous sodium sulfate drying organic layer is used, filter, concentrating under reduced pressure obtains 1 of the replacement of N2-glycosyl, 2, the hydrolysate of 3-triazole class compounds.
- 8., by the preparation method of the 1,2,3-triazoles compounds of the N2-glycosyl replacement described in claim 6 or 7, it is characterized in that described solvent is DMF, DMSO or acetonitrile.
- 9., by the preparation method of the 1,2,3-triazoles compounds of the N2-glycosyl replacement described in claim 6 or 7, it is characterized in that described alkali is salt of wormwood or sodium carbonate.
- 10., by the preparation method of the 1,2,3-triazoles compounds of the N2-glycosyl replacement described in claim 6 or 7, it is characterized in that described diluted acid is sulfuric acid.
- The 1,2,3-triazoles compound that N2-glycosyl described in 11. claims 1 or 2 replaces is as the application of the paramedicines of diabetes B.
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| CN105566235A (en) * | 2016-03-03 | 2016-05-11 | 武汉工程大学 | Method for synthesizing NH-1,2,3-triazole in steps by utilizing catalysis of aluminium salt |
| CN112961196A (en) * | 2021-02-07 | 2021-06-15 | 中国人民大学 | Preparation method of 1,2, 3-triazole compound modified by glycosyl and polypeptide |
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| BRPI0804764A2 (en) * | 2008-07-28 | 2010-07-27 | Univ Rio De Janeiro | alpha-glycosity inhibitors, pharmaceutical compositions comprising them and process for their preparation |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105566235A (en) * | 2016-03-03 | 2016-05-11 | 武汉工程大学 | Method for synthesizing NH-1,2,3-triazole in steps by utilizing catalysis of aluminium salt |
| CN112961196A (en) * | 2021-02-07 | 2021-06-15 | 中国人民大学 | Preparation method of 1,2, 3-triazole compound modified by glycosyl and polypeptide |
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Application publication date: 20160113 |